Coumarin derivatives

Short description: Organic compounds derived from coumarin

"Coumarins" redirects here. For the class of anticoagulants and rodenticides specifically, see 4-Hydroxycoumarins. For the parent compound, see Coumarin.

Chemical structure of coumarin

Coumarin derivatives are derivatives of coumarin and are considered phenylpropanoids.[1] Among the most important derivatives are the 4-hydroxycoumarins, which exhibit anticoagulant properties, a characteristic not present for coumarin itself.

Some naturally occurring coumarin derivatives include umbelliferone (7-hydroxycoumarin), aesculetin (6,7-dihydroxycoumarin), herniarin (7-methoxycoumarin), psoralen and imperatorin.

4-Phenylcoumarin is the backbone of the neoflavones, a type of neoflavonoids.

Coumarin-pyrazole hybrids have been synthesized from hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction. Whereas, coumarin-pyridine hybrids have been prepared from the Knoevenagel condensation of pyridylacetontriles with substituted salicylaldehydes.[2]

Compounds derived from coumarin are also called coumarins or coumarinoids; this family includes:

* brodifacoum[3][4]
* bromadiolone[5]
* difenacoum[6]
* auraptene
* ensaculin
* phenprocoumon (Marcoumar)
* PSB-SB-487
* PSB-SB-1202
* scopoletin can be isolated from the bark of Shorea pinanga[7]
* warfarin (Coumadin)

Coumarin is transformed into the natural anticoagulant dicoumarol by a number of species of fungi.[8] This occurs as the result of the production of 4-hydroxycoumarin, then further (in the presence of naturally occurring formaldehyde) into the actual anticoagulant dicoumarol, a fermentation product and mycotoxin. Dicoumarol was responsible for the bleeding disease known historically as "sweet clover disease" in cattle eating moldy sweet clover silage.[8][9] In basic research, preliminary evidence exists for coumarin having various biological activities, including anti-inflammatory, anti-tumor, antibacterial, and antifungal properties, among others.[8]

## Contents

* 1 Uses
* 1.1 Medicine
* 1.2 Laser dyes
* 2 References

## Uses

### Medicine

Warfarin - a coumarin - with brand name, Coumadin, is a prescription drug used as an anticoagulant to inhibit formation of blood clots, and so is a therapy for deep vein thrombosis and pulmonary embolism.[10][11][12] It may be used to prevent recurrent blood clot formation from atrial fibrillation, thrombotic stroke, and transient ischemic attacks.[12]

Coumarins have shown some evidence of biological activity and have limited approval for few medical uses as pharmaceuticals, such as in the treatment of lymphedema.[10][13] Both coumarin and 1,3-indandione derivatives produce a uricosuric effect, presumably by interfering with the renal tubular reabsorption of urate.[14]

### Laser dyes

Arising from tunable intramolecular charge transfer (ICT) properties within the molecule, coumarins have found purpose as dyes and stains, particularly those featuring electron-donating substituents at the 7-position, which can be used to enhance this behavior. Coumarin dyes are extensively used as gain media in blue-green tunable organic dye lasers.[15][16][17] Among the various coumarin laser dyes are coumarins 480, 490, 504, 521, 504T, and 521T.[17] Coumarin tetramethyl laser dyes offer wide tunability and high laser gain,[18][19] and they are also used as active medium in coherent OLED emitters.[20][15][16][17] and as a sensitizer in older photovoltaic technologies.[21]

## References

1. ↑ Jacobowitz, Joseph R.; Weng, Jing-Ke (2020-04-29). "Exploring Uncharted Territories of Plant Specialized Metabolism in the Postgenomic Era". Annual Review of Plant Biology (Annual Reviews) 71 (1): 631–658. doi:10.1146/annurev-arplant-081519-035634. ISSN 1543-5008. PMID 32176525.
2. ↑ Burden, Thomas J.; Fernandez, Kathryn P. R.; Kagoro, Mary; Eastwood, Jonathan B.; Tanner, Theo F. N.; Whitwood, Adrian C.; Clark, Ian P.; Towrie, Michael et al. (2023). "Coumarin C−H Functionalization by Mn(I) Carbonyls: Mechanistic Insight by Ultra-Fast IR Spectroscopic Analysis" (in en). Chemistry – A European Journal 29 (25): e202203038. doi:10.1002/chem.202203038. ISSN 1521-3765. PMID 36625067. PMC 10947090. https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202203038.
3. ↑ International Programme on Chemical Safety. "Brodifacoum (pesticide data sheet)". http://www.inchem.org/documents/pds/pds/pest57_e.htm.
4. ↑ Laposata, M; Van Cott, E. M.; Lev, M. H. (2007). "Case 1-2007—A 40-Year-Old Woman with Epistaxis, Hematemesis, and Altered Mental Status". New England Journal of Medicine 356 (2): 174–82. doi:10.1056/NEJMcpc069032. PMID 17215536.
5. ↑ International Programme on Chemical Safety. "Bromadiolone (pesticide data sheet)". http://www.inchem.org/documents/pds/pds/pest88_e.htm.
6. ↑ International Programme on Chemical Safety. "Difenacoum (health and safety guide)". http://www.inchem.org/documents/hsg/hsg/hsg095.htm.
7. ↑ Syah, Y. M. (2009). "A modified oligostilbenoid, diptoindonesin C, from Shorea pinanga Scheff". Natural Product Research 23 (7): 591–594. doi:10.1080/14786410600761235. PMID 19401910.
8. ↑ 8.0 8.1 8.2 Venugopala, K. N.; Rashmi, V; Odhav, B (2013). "Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity". BioMed Research International 2013: 1–14. doi:10.1155/2013/963248. PMID 23586066.
9. ↑ Bye, A.; King, H. K. (1970). "The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius". Biochemical Journal 117 (2): 237–45. doi:10.1042/bj1170237. PMID 4192639.
10. ↑ 10.0 10.1 "Coumarin". PubChem, National Library of Medicine, US National Institutes of Health. 4 April 2019. https://pubchem.ncbi.nlm.nih.gov/compound/323.
11. ↑ "Coumarins and indandiones". Drugs.com. 2016. https://www.drugs.com/drug-class/coumarins-and-indandiones.html.
12. ↑ 12.0 12.1 "Warfarin". Drugs.com. 7 March 2019. https://www.drugs.com/ppa/warfarin.html.
13. ↑ Farinola, N.; Piller, N. (June 1, 2005). "Pharmacogenomics: Its role in re-establishing coumarin as treatment for lymphedema". Lymphatic Research and Biology 3 (2): 81–86. doi:10.1089/lrb.2005.3.81. PMID 16000056.
14. ↑ Christensen, Flemming (1964-01-12). "Uricosuric Effect of Dicoumarol". Acta Medica Scandinavica 175 (4): 461–468. doi:10.1111/j.0954-6820.1964.tb00594.x. ISSN 0954-6820. PMID 14149651.
15. ↑ 15.0 15.1 Schäfer, F. P., ed (1990). Dye Lasers (3rd ed.). Berlin: Springer-Verlag. [ISBN missing]
16. ↑ 16.0 16.1 Duarte, F. J.; Hillman, L. W., eds (1990). Dye Laser Principles. New York: Academic. [ISBN missing]
17. ↑ 17.0 17.1 17.2 Duarte, F. J. (2003). "Appendix of Laser Dyes". Tunable Laser Optics. New York: Elsevier-Academic. [ISBN missing]
18. ↑ Chen, C. H.; Fox, J. L.; Duarte, F. J. (1988). "Lasing characteristics of new-coumarin-analog dyes: broadband and narrow-linewidth performance". Appl. Opt. 27 (3): 443–445. doi:10.1364/ao.27.000443. PMID 20523615. Bibcode: 1988ApOpt..27..443C.
19. ↑ Duarte, F. J.; Liao, L. S.; Vaeth, K. M.; Miller, A. M. (2006). "Widely tunable laser emission using the coumarin 545 tetramethyl dye as gain medium". J. Opt. A 8 (2): 172–174. doi:10.1088/1464-4258/8/2/010. Bibcode: 2006JOptA...8..172D.
20. ↑ Duarte, F. J.; Liao, L. S.; Vaeth, K. M. (2005). "Coherence characteristics of electrically excited tandem organic light-emitting diodes". Opt. Lett. 30 (22): 3072–3074. doi:10.1364/ol.30.003072. PMID 16315725. Bibcode: 2005OptL...30.3072D.
21. ↑ Loutfy et al., US patent 4175982, issued Nov. 27, 1978, assigned to Xerox Corp

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